Holiday rentals in Flossmoor

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

Fore! Peace & Love @ Golf House

Welcome to "The Golf House"! Our 4-bed, 3-bath home sleeps 8 people comfortably and, features an open living space with a stunning golf course view, a full kitchen, and a huge deck. Enjoy natural sunlight or the stars through the skylight both in the master bedroom and bathroom. The home has hardwood floors, and TVs in each bedroom. Plus, a heated meditation room for relaxation. Ideal for families, women retreats, networking events etc. Experience luxury and tranquility right by the greens!

Cozy & Lavish 2B/1B in Homewood!

Our Peaceful and Centrally-located Duplex sits in the heart of Downtown Homewood. The choice of a 30 min drive or 7 min walk to the Metra going to Downtown Chicago awaits you! You can enjoy this vacation home while exploring the beautiful city! Our new Casino welcomes you! Enjoy the convenience of free parking, nearby shopping markets and quick access quick to I-57, I-80, I-94, & I-294. Long-Term Travel Stays are Welcomed! ( Nearby hospitals include UCM, Advocate, Franciscan, & Rush)

Spacious and Cozy Oasis Close to Fun

Escape to our inviting 2nd-floor High-End condo, just a short 37-minute drive from the vibrant heart of Downtown Chicago, Millennium Park, and Navy Pier. Immerse yourself in the charm of our neighborhood, surrounded by custom homes, golf clubs, and family-friendly entertainment. Many dining options all within a 2-minute drive or a quick Uber ride. Large balcony with seating for six and 2 minutes from the Metra Train Station for a fast trip to Chicago. Be one of our first guests!

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Modern Charming Home w/Pergola & games

➜ Fully remodeled 3 beds, 2 bath home with modern finishes ➜ Spacious backyard with, pergola, seating areas, and outdoor games ➜ Smart TVs in every room ➜ Game room with pool table, ping pong and family games ➜ Large private backyard with pergola, seating areas and outdoor playgrounds.

The Attic

Neat and Clean. Short walk to Metra Train Station to Chicago LaSalle Street Station. Queen Size bed with twin air mattress available upon request. The Attic as you might guess is on the second floor. Will have to go up one flight of stairs (see pictures).

Comfy Apt Made For Professionals or Couples

Quiet apartment perfect for working professionals and couples who would like a cozy home away from home. It has everything you would need to make your stay comfortable with a washer, dryer, full kitchen, and cable TV. Easy commute to Chicago.